DPA-Substituted Carbazole Derivative as a Fluorescent Ligand for G4†DNA.

ABSTRACT

Herein a conjugated dipicolylamine/carbazole (Car-DPA) molecule was designed and synthesized to enhance the performance for the application as a G4 fluorescent ligand. This ligand has been found to display distinct and specific fluorescence enhancements in the presence of various G4 DNA structures, but limited with ssDNA or dsDNAs. The detail binding characteristics of the ligand with c-MYC G4 DNA were investigated by fluorescence, UV/VIS absorption, CD spectroscopy, and molecular docking. The present study demonstrated that Car-DPA bound to c-MYC G4s with a two-step complex formation, in which the binding mode appeared to be end-stacking. Confocal fluorescence images indicated that ligand Car-DPA could locate in nucleus, which is quite prominent from the cellular internalization studies.